Benzylidene indandione compound and preparation thereof and application in specific imaging of lipid droplet

A technology of benzylidene indanedione and compound is applied in the application field of lipid droplet-specific fluorescence imaging, which can solve the problems of limited application, aggregation-induced quenching, high cost, etc., and achieves large Stokes shift and low cytotoxicity. , easy-to-prepare effects

Active Publication Date: 2017-05-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to realize lipid droplet-specific fluorescence imaging, the following key issues need to be solved: (1) In order to achieve high-brightness fluorescence imaging of lipid droplets, fluorescent materials need to be aggregated in lipid droplets at high concentrations, however, the aggregation-induced quenching of traditional fluorescent materials The disadvantages of these severely limit their application in high-brightness lipid droplet fluorescence imaging; (2) in order to reduce production costs, it is necessary to develop easily prepared lipid droplet-specific fluorescent probes
However, traditional lipid droplet-specific fluorescent probes require multi-step synthesis, are difficult to prepare, and are expensive; (3) lipid droplet-specific fluorescent probes should have a large two-photon absorption cross-section in the near-infrared region. Photon-excited fluorescence imaging can effectively reduce background noise, reduce light damage, and improve deep penetration ability; (4) lipid droplet-specific fluorescent probe molecules should have rapid penetration ability of living cells, which is convenient for imaging applications; (5) Strong photostability, convenient for long-term continuous observation, however, traditional fluorescent materials are prone to photobleaching, making it difficult to use for continuous observation

Method used

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  • Benzylidene indandione compound and preparation thereof and application in specific imaging of lipid droplet
  • Benzylidene indandione compound and preparation thereof and application in specific imaging of lipid droplet
  • Benzylidene indandione compound and preparation thereof and application in specific imaging of lipid droplet

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Benzylidene indenedione compound IND-TPA: 2-(4-(diphenylamino)benzylidene)-1H-indene-1,3(2H)-dione (R 1 = Hydrogen, R 2 =R 3 =Phenyl) The structural formula is as follows:

[0053]

[0054] The preparation method of the above-mentioned benzylidene indenedione compound includes the following steps:

[0055] 4-Diphenylaminobenzaldehyde (273mg, 1.0mmol), 1,3-indenedione (146mg, 1.0mmol) and morpholine (85mg, 1.0mmol) were dissolved in 15mL of ethanol, followed by refluxing under nitrogen protection (Reaction at 78°C for 3 hours); after the reaction is over, return to room temperature, filter and vacuum dry to obtain the red solid product 2-(4-(diphenylamino)benzylidene)-1H-indene-1,3( 2H)-Diketone (285 mg, 71% yield). The relevant structural characterization data are as follows:

[0056] 1 H NMR(DMSO-d 6 ,500MHz): δ8.49(d,J=9.0Hz,2H),7.93-7.89(m,4H),7.71(s,1H),7.48-7.45(m,4H),7.30-7.26(m,6H) ), 6.85(d,J=9.0Hz,2H); 13 C NMR(CD 2 Cl 2 ,125MHz):191.3,189.6,152.7,146.6,145.8,142.4...

Embodiment 2

[0058] Characterization of the photophysical properties of the compound IND-TPA prepared in Example 1:

[0059] Combine tetrahydrofuran and water in different volume ratios (tetrahydrofuran: water = 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, 1:99) to form the water content (f w ) Different mixtures, dissolve the compound IND-TPA into these mixtures to make the concentration of the compound 10 -5 mol·L -1 , And then detect the fluorescence emission spectrum and the ultraviolet absorption spectrum in tetrahydrofuran, the result is figure 1 . figure 1 The UV absorption and fluorescence emission spectra of the compound IND-TPA prepared in Example 1; (A) the normalized UV absorption spectrum of the compound IND-TPA in tetrahydrofuran; (B) the compound IND-TPA in tetrahydrofuran and water Fluorescence emission spectra of increasing water content in the mixed solution (10 - 5 mol·L -1 ); (C) is the ratio of the maximum fluorescence emission intensity of compoun...

Embodiment 3

[0067] Cytotoxicity test of the compound IND-TPA prepared in Example 1:

[0068] The experimental results of the cytotoxicity of the compound IND-TPA against lung cancer cells HCC827 and A549 are as follows Figure 5 Shown. This result shows that the compound IND-TPA has almost no cytotoxicity at different concentrations (5, 10, 20, 40, 60, 80, 100 μM).

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Abstract

The invention belongs to the field of medical materials, and discloses a benzylidene indandione compound and a preparation thereof and an application in specific imaging of a lipid droplet. The structure of the benzylidene indandione compound is as shown in a formula I. The benzylidene indandione compound has the advantage of aggregation-induced emission, and the defects of aggregation-induced quenching of a traditional fluorescent dye can be effectively overcome, so that the specific fluorescence imaging of the lipid droplet in a living cell can be achieved; furthermore, the benzylidene indandione compound has a two-photon absorption cross-section which is high in living cell penetration rate, high in signal to noise ratio, small in cytotoxicity, large in stokes shift and large in near infrared region. The formula I is as shown in the specification.

Description

Technical field [0001] The invention belongs to the field of medical materials, and specifically relates to a compound with aggregation-induced luminescence properties, a preparation method thereof, and application in lipid droplet specific fluorescence imaging. Background technique [0002] Lipid droplets are not only an important storage place for lipid molecules and proteins, but also a dynamically changing multifunctional organelle. The size and number of lipid droplets vary greatly among different cells. Since lipid droplets can not only serve as energy storage, but also play an important role in membrane synthesis and protein degradation. Lipid droplets are closely related to many diseases, including cancer, inflammation, viral infection and obesity. [0003] Cancer cells have the characteristics of rapid proliferation, so there is a high demand for lipid molecules such as fatty acids and phospholipids, and the corresponding lipid droplet content in cancer cells is also sign...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/22C09K11/06G01N21/64
CPCC07C225/22C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014G01N21/6486
Inventor 唐本忠高蒙秦安军
Owner SOUTH CHINA UNIV OF TECH
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